How Much Does It Cost To Fly To Chicago?

The cheapest tickets to Chicago available within the past 7 days were $101. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chicago Flights

Chicago Airports

When youíre looking to book flights to Chicago, Illinois, there are two airports that serve the Windy City. O'Hare International Airport is the main one, while Chicago Midway International Airport is considered the secondary tarmac.

O'Hare sits 17 miles northwest of the Loop. It provides plenty of amenities to keep you entertained while you wait for your flight or transportation into Chi-Town. If youíre hungry, youíre in luck. This airport boasts a variety of restaurants and cafes, providing sit-down cuisine and meals-on-the-go. The airport also features various shops, where you can find Chicago souvenirs, designer goods, electronics, and duty-free products. To top it all off, O'Hare provides spa services and even a yoga room to help keep you relaxed and rejuvenated during your travels. Find out additional information about O'Hare on Flights.com.

Located roughly 12 miles northwest of downtown Chicago, Midway Airport includes several shops, the majority of which are located in the Midway Boulevard. You can also find restaurants, snack shops, and fast-food options when youíre looking fuel up before or after your flight. While youíre traveling through the airport, look for the public art and installation collections throughout the terminal.

Airport Transportation

When you have Chicago flights, rest assured knowing that both airports provide ground transportation. Here at Expedia.com, you can reserve Chicago car rentals and pick up your vehicle at your preferred airport. Alternatively, you can take advantage of public transportation as the Chicago Transit Authority provides both train and bus service to Midway and OíHare. Other transportation options include taxis, shuttles, and limousines.

Chicago Activities

Once youíve decided itís time to book plane tickets to Chicago, IL, start planning your adventures. The Windy City is home to fascinating exhibits, from the galleries at the Museum of Contemporary Art to the artifacts at the Chicago History Museum. For some of the best views of the skyline, venture up to the 360 Chicago observatory deck in the John Hancock building or the Skydeck Chicago in the Willis Tower. While youíre in town, chow down on some famous deep-dish pizza or Chicago-style hot dogs for an authentic taste of the city. Then round out your day with reservations at one of the best hotels in Chicago.

Planning Your Trip

The best times to visit Chicago are between April and May and September and October. Temperatures are moderate during these months, and the high season hasnít hit yet. Summertime is considered the most popular time to visit, so you may face more crowds and more expensive rates during this season. Meanwhile, winter brings temperatures in the low 30s F and a high chance of snowstorms.

Regardless of when you plan to visit, Expedia.com is here to match you with cheap flights to Chicago. Sort through our selection to find discounts on round-trip tickets that suit your price range. You can even use our mobile booking app for convenient access to exclusive online deals on airfare to Chicago. Book your affordable flights right here and start getting a taste for that delicious deep-dish pizza.

Get up to 100% off your flight to Chicago when booking a Flight + Hotel

Reviews from verified customers

We were able to pay for an upgrade. Service and comfort was outstanding. Thank you! I would fly Norwegian again anytime.

A verified traveler

London to Chicago · Norwegian Air UK

Mar 21, 2019

Happy overall, but I do have to point out that the leg room seems to be getting smaller

A verified traveler

San Antonio to Chicago · American Airlines

Mar 21, 2019

A big thank you to the Chicago staff that rearranged our seats so our family could sit by each other and holding the flight two extra minutes so we could make our connecting flight!!

A verified traveler

Milwaukee to Chicago · United

Mar 21, 2019

We came in early!

A verified traveler

San Juan to Chicago · United

Mar 21, 2019

Flight was delayed 5 hours

A verified traveler

Rochester to Chicago · United

Mar 21, 2019

Flight was delayed in Denver because of a blizzard two days before, so we were late getting into Chicago. I only had less than 20 minutes to stint from terminal 1 to terminal 2. Was sure my bag would not make the flight, but much to my surprise it did.

A verified traveler

Denver to Chicago · United

Mar 21, 2019

Would love biscoff cookies instead of pretzels for the inflight snack.

A verified traveler

Tulsa to Chicago · United

Mar 21, 2019

Wasnt happy I had to pay for check in bag before I could get boarding pass

A verified traveler

Las Vegas to Chicago · United

Mar 20, 2019

So grateful for United. I’m a nervous flyer and the staff was so kind. They treated my 9 year old very well also. Thankful for the smooth flight and great people!